A New Synthesis of 2-[(Dialkylcarbamoyl)Methylene]Tetrahydrofuran Derivatives by Pd-Catalyzed Oxidative Aminocarbonylation of 4-yn-1-ols

Author(s): Bartolo Gabriele, Giuseppe Salerno, Pierluigi Plastina.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 2 , 2004

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Abstract:

A novel synthesis of 2-[(dialkylcarbamoyl)methylene]tetrahydrofuran derivatives 3-8 by Pd-catalyzed oxidative carbonylation of 4-yn-1-ols 1 in the presence of dialkylamines 2 is reported (2:1 molar ratio = 2). Reactions are carried out in 1,2- dimethoxyethane (DME) at 100°C and under 20 atm (at 25°C) of a 4:1 mixture of CO and air, in the presence of catalytic amounts of PdI2 (1 mol % with respect to 1) in conjunction with 10 equiv. of KI. Formation of 3-8 occurs through Pd-catalyzed oxidative monoaminocarbonylation of the triple bond of 1 to give 6-hydroxy-2-ynamide intermediates 9, followed by stereoselective conjugate addition of the hydroxyl group to the triple bond.

Keywords: aminocarbonylation, carbonylation, methylene]tetrahydrofurans, palladium

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Article Details

VOLUME: 1
ISSUE: 2
Year: 2004
Page: [134 - 136]
Pages: 3
DOI: 10.2174/1570178043488437
Price: $58